Escort

Chapter 1

"Are you ready yet?" Tom asked for the third time.

He sat on the bed staring into the bathroom as I did my face.
I slapped my lipstick down on the counter and rolled my eyes.

There was a sigh let out before I walked over to him and leaned down. I held his face in both of my hands to kiss him sweetly.

"Is that what you wanted?" I asked as I wiped his bottom lip that now had a smudge of my lipstick.
He looked at my lips. "Another one?" he begged.
I gave him a small peck. "No more than that. I have to finish getting ready. You want me to look pretty at your dinner, don't you?"
"Yea, but..."
"So you're going to sit here, and you're going to wait and be obedient for me." I interrupted. "Maybe later we'll do what you like."
"Really?" he wondered.
"Only if you're a good boy while I finish my makeup." I stood up straight and walked back into the bathroom.
"Okay..."

Tom Hathaway. CEO of some company that manufactures sporting goods. He's about 48 years old, not married, zero kids, and I'm his escort tonight for a dinner he's hosting. I always wonder how much less seriously he'd be taken if they found out he liked being pegged and called a good boy. Honestly, I find humor in when he attempts to control me in public. Only to later have me slap him around with a whip as he whimpers and apologizes.

Tonight's the last night I work with him, so I guess I'll have to do something special.

I did the finishing touches to my lipstick then capped it and walked back out.
"Okay, let's go." I permitted.
He stood up and reached for my hand.
I looked at him.
"Please..." he begged.
I put my hand in his and we walked out of the hotel room.

____________________________________

We made it to the dining hall where the dinner was being hosted.

Every so often, Tom would wrap his arm around my waist as he laughed and spoke to partners and shareholders.
I just stood there looking pretty like I always did.

I may stand next to a client with an expression seemingly as if I wish I wasn't but I do actually love my job. It's so easy. I ask for what I want and I get it with the opportunity of dominating men in power. You have no idea how good it feels to watch a man say women can't do his job then be able to call him a disgusting bitch. While he begs me to let him cum...

and I tell him no.

"I'm going to get something to drink, okay?" I told Tom.
"Okay, my dear." he replied and kissed my cheek.
I walked off towards the bar.

When I got there I turned to see him and he wasn't paying attention to me so I quietly slipped away.

I walked to the back and out of the door.

I stood against the brick wall and dug into my purse. Finding the cigarette carton I'd left in there.
I pulled one out and found my lighter.

I lit it but soon remembered I'm supposed to be quitting. I flung it onto the ground and took a deep breath.

I decided instead I could just call my father to cure my boredom.
But he should be getting ready for bed around this time.

I took out my phone to begin dialing.

"Evening." someone greeted.

I looked to the side. He was older but he was handsome.

"Hi." I said and faced him.
"You are?" He held his hand out.
"Leilani. You?" I didn't give him my real name or my hand. He didn't need to know that and also...germs.
He closed his palm. "Tony. It's nice to meet you."
"You as well."

He looked at the ground, eyes landing on the cigarette I'd wasted.

"There goes fifteen cents." he stated.
"Hopefully more than that later." I added.
He looked back at me.
"I'm trying to quit."
"Ah." he nodded as he understood.
"Can I help you with something, Tony?"
"You're here with Tom Hathaway, correct?"
"That is correct, yes."
"Hm." He stared off.
"Is there something else or do you just have a knack for stating the obvious?"
"How much did that cost him?"
I snickered. "How do you know it cost him anything?"
"Look at you."
I scoffed.
"Beautiful. Tall. Modelesque. You don't look a day over 21, honestly."

I looked at him as he described me.

"So?" he stated.
"So, what?"
"How much?" he questioned.
"Why do you want to know so badly?" I smiled.
He looked at me.

I giggled to myself then leaned against the wall and stared at the night sky as I calculated the math.

"About...twenty grand."
"Twenty grand?!" he repeated in awe.
I looked at him. "Mhm."
"For what?"
"Well, he paid extra for a few kinks. Wanting me to sleep in the same bed as him, he's a very lonely guy. And he also bought this dress for me and the accessories. All of that plus the original cost sums to 20 grand."
"So it's 20 grand if they want to spoil you?"
"You could say that. The original price is about 5-10 depending on what you order. Over the years, price has gone up with demand. You have no idea how high my demand is."
"Hm..."
"I'm assuming you need something." I said sweetly.

He was actually one of the more handsome older men I'd ever seen. He was grey with a few brown or black streaks still hanging on. It was dark out so I couldn't tell which color specifically. He had a neatly trimmed beard and mustache. His teeth were straight and white. He was tall. I'd actually be comfortable being his escort, some men have to spend a few days trying to convince me. But he was attractive. To be honest, I wondered why he needed an escort to begin with.

"I have a gala I need to go to in a few days." he began as he looked through the alleyway.
"Mhm..."
"I want you to accompany me but I also want us to get to know each other beforehand. So that the gala is smooth sailing. If I don't know you, we won't look comfortable, and then it'll be obvious."
"How many days beforehand?"
"About three or four..." he shrugged.
I thought about all of my packages.
"How much would that be?" he asked and looked back at me.

"Around 8 grand." I stated.
"Really?"
"Well, I have a long list of people who need me. You're cutting the line, it's short notice,..." I realized something. "Do you want intimacy?" I asked.
He looked away again like he was thinking and embarrassed of his answer.
He shrugged. "Well...I mean...if it comes with it then I..."
I snickered. It was cute that he was shy about it.

I gently held his jaw in my hand and made him look back at me.

"I'll tell you what, okay?"
He looked at my lips as he nodded slowly.
"You're one of my cuter clients so I'll cut you a deal. You'll get me wrapped around your arm...a few dates before hand...and orgasms so good you'll think you're young again, all for only 8,500."
"8500?"
"Baby, I'll need a place to stay, dress, jewelry, the excess is expenses you have to pay so I can be properly ready and taken care of for when the time comes. There's tiers to this. I'm top tier. I'm not a hooker off the street just doing this for $200 to buy crack, I got men with twice your income asking me to be a date to the Oscars." My thumb grazed over his bottom lip.

I let him free and went into my purse. In it, I found one of my cards. On it, was my job description and number. I never had a name written on it since I always gave a different name to different men.

I kissed it, leaving a lipstick stain and handed it over.
"Call me when you decide what you want." I instructed.
He took it and I walked back inside.